Organic compound and application thereof, and organic electroluminescent device containing organic compound

Abstract

The invention provides an organic compound and application thereof, and an organic electroluminescent device comprising the same, the organic compound has a structure as shown in a formula I. Through design and mutual compounding of a boron-nitrogen multiple resonance mother nucleus structure and a specific pyrene group RX, the organic compound plays roles in reducing triplet state energy level and adjusting light color, and the organic electroluminescent device has the advantages that the organic electroluminescent device can be used for reducing the triplet state energy level and adjusting the light color; the organic compound has excellent electroluminescent performance, can give triplet excitons to realize high luminous efficiency, is suitable for being used as a luminescent dye, especially a green luminescent dye, can effectively improve the carrier transport efficiency, and can be used as a green luminescent dye. The organic light-emitting device comprising the organic light-emitting material has higher light-emitting efficiency, longer service life and lower voltage, the comprehensive performance of the device is improved, and the requirements for high-performance materials in current panel and display manufacturing are fully met.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic compound and application thereof, and an organic electroluminescent device containing the organic compound. Background Art

[0002] In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them very suitable for manufacturing on flexible substrates. Beautiful and cool optoelectronic products can be designed and produced according to demand, gaining unparalleled advantages over inorganic materials. Examples of organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, OLED has developed particularly rapidly and has achieved commercial success in the field of information display. OLED can provide highly saturated red, green, and blue colors. Full-color display devices made of OLEDs do not require additional backlight sources and have the advantages of brilliant colors, lightness, thinness, and softness.

[0003] The core of OLED devices is a thin film structure containing a variety of organic functional materials. Common organic functional materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, luminescent host materials and luminescent guest materials (dyes), etc. When the OLED device is powered on, electrons and holes are injected and transported to the luminescent area and recombine there, thereby generating excitons and emitting light.

[0004] In recent years, people have developed a variety of organic materials, combined with various device structures, which can improve carrier mobility, regulate carrier balance, break through electroluminescence efficiency, and delay device attenuation. For quantum mechanical reasons, common fluorescent luminescent bodies mainly use singlet excitons generated when electrons and holes combine to achieve luminescence, and are still widely used in various OLED products. Some metal complexes (such as iridium complexes) can simultaneously use triplet excitons and singlet excitons to emit light, which are called phosphorescent luminescent bodies. Their energy conversion efficiency can be increased by up to four times that of traditional fluorescent luminescent bodies. Thermally excited delayed fluorescence (TADF) technology promotes the transformation of triplet excitons to singlet excitons. Without the use of metal complexes, triplet excitons can still be effectively utilized to achieve higher luminescence efficiency. Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize luminescent bodies by energy transfer, which can also achieve higher luminescence efficiency. TADF and TASF have very broad application prospects in the field of blue luminescence, which has always been difficult to effectively improve luminescence efficiency.

[0005] Under the condition of electrical excitation, organic electroluminescent devices will produce 25% singlet excitons and 75% triplet excitons; traditional fluorescent materials can only use 25% of singlet excitons due to spin prohibition, so the external quantum efficiency is limited to less than 5%. Almost all triplet excitons can only be lost in the form of heat. In order to improve the efficiency of organic electroluminescent devices, triplet excitons must be fully utilized. To this end, researchers have proposed many methods, the most notable of which is the use of phosphorescent materials. Phosphorescent materials introduce heavy atoms and have a spin-orbit coupling effect, which can fully utilize 75% of triplet excitons and achieve 100% internal quantum efficiency. However, phosphorescent materials use rare heavy metals, which makes the materials expensive and is not conducive to cost control. If fluorescent devices can make good use of triplet excitons, this problem can be effectively solved. Researchers have proposed a method to improve the efficiency of fluorescent devices by quenching triplet excitons to produce singlet excitons in fluorescent devices, but the maximum external quantum efficiency that this method can theoretically achieve is only 62.5%, which is much lower than that of phosphorescent materials. Therefore, it is very necessary to find new technologies to make full use of the triplet energy levels of fluorescent materials to improve the luminescence efficiency. This field is in urgent need of developing fluorescent organic electroluminescent materials with better performance. Summary of the invention

[0006] In view of the deficiencies in the prior art, the purpose of the present invention is to provide an organic compound and its application, and an organic electroluminescent device containing the same. Through the design of the molecular structure, the excellent electroluminescent performance, luminous efficiency and life characteristics of the organic compound are made more balanced. It is used in organic electroluminescent devices and can be used as a fluorescent doping material for the light-emitting layer, which can effectively improve the comprehensive performance of the device.

[0007] To achieve this object, the present invention adopts the following technical solutions:

[0008] In a first aspect, the present invention provides an organic compound having a structure as shown in Formula I:

[0009]

[0010] In Formula I, X1, X2, X3, and X4 are each independently selected from CR A1 or N; multiple (e.g. 2, 3, 4) CR A1 R A1 are the same or different groups.

[0011] In Formula I, Y1, Y2, Y3, and Y4 are each independently selected from CR A2 or N; multiple (e.g. 2, 3, 4) CR A2 R A2 are the same or different groups.

[0012] In Formula I, Z1, Z2, and Z3 are each independently selected from CR A3 or N; multiple (e.g. 2, 3) CR A3 R A3 are the same or different groups.

[0013] R A1 , R A2 , R A3 Each is independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0014] In Formula I, Ar1 and Ar2 are each independently selected from unsubstituted or R B Substituted C6-C60 aryl, unsubstituted or R B Any one of the substituted C3-C60 heteroaryl groups; Ar1 ​​and Ar2 are each independently not connected to the adjacent ring structure or are connected to form a ring through a chemical bond.

[0015] In the present invention, "Ar1 is not connected to the adjacent ring structure" means that Ar1 is only connected to the N atom through a single bond; "Ar1 is connected to the adjacent ring structure through a chemical bond to form a ring" means that Ar1 is connected to the N atom through a chemical bond and is also connected to the adjacent ring (such as the ring where X4 is located) through a chemical bond, thereby forming a fused ring structure; the relevant description of Ar2 is similar. When the same description is involved below, it has the same meaning and will not be repeated one by one.

[0016] R BEach is independently selected from any one of halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0017] Any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 Any two adjacent R B At least one group of them is connected by a chemical bond to form ring E, and the ring E is selected from any one of substituted or unsubstituted C3-C60 heteroaromatic rings.

[0018] It should be noted that in the present invention, “any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 Any two adjacent R B " preferably refers to any two adjacent groups located in the same six-membered ring.

[0019] The R A1 , R A2 , R A3 , R B In the above, the other groups except those forming the ring E are each independently not connected to the adjacent ring structure or are connected to form a ring through a chemical bond.

[0020] R A1 , R A2 , R A3 , Ring E, R BThe substituted substituents are each independently selected from halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 arylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano , nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.

[0021] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple (at least 2) substituents, they may be the same or different substituents. When the same expressions are mentioned below, they have the same meaning. Unless otherwise specified, the selection range of substituents is as shown above and will not be repeated.

[0022] The R A1 , R A2 , R A3 At least one of the groups is R X , and / or, the R B At least one of the groups is R X .

[0023] It should be noted that in the organic compound of the present invention, the fused ring structure is connected to at least one R X , the R X It can be connected to the C atom where X1, X2, X3, X4, Y1, Y2, Y3, Y4, Z1, Z2, and Z3 are located, or it can be connected to the C atom in Ar1 and Ar2 as a substituent in Ar1 and Ar2.

[0024] The R X for Represents the attachment site of the group.

[0025] L is selected from any one of a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group; when L is a single bond, it means that the pyrene group (carbon atom on the condensed ring) is directly connected to the C atom where X1, X2, X3, X4, Y1, Y2, Y3, Y4, Z1, Z2, and Z3 are located through a single bond, or the pyrene group (carbon atom on the condensed ring) is directly connected to the C atom in Ar1 and Ar2 through a single bond as a substituent in Ar1 and Ar2, and the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring through a chemical bond.

[0026] R 1 , R 2 Each independently represents no substitution, mono-substitution to the maximum permissible substitution; specifically, R 1 Indicates no substitution (R 1 is hydrogen), monosubstituted, disubstituted, trisubstituted or tetrasubstituted; when R 1 When multiple substitutions are indicated, multiple R 1 are the same or different groups; R 2 Indicates no substitution (R 2 is hydrogen), monosubstituted, disubstituted, trisubstituted, tetrasubstituted or pentasubstituted; when R 2 When multiple substitutions are indicated, multiple R 2 are the same or different groups. 1 , R 2 Preferably it means unsubstituted or monosubstituted.

[0027] R 1 , R 2 Each is independently selected from any one or a combination of at least two of hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0028] The substituted substituents in L are each independently selected from any one of halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.

[0029] R' is independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, or a combination of at least two thereof; adjacent R's are not connected or are connected to form a ring by chemical bonds; the R' is not connected to adjacent ring structures or is connected to form a ring by chemical bonds.

[0030] In the present invention, the "unsubstituted or R'substituted" group may be substituted with one substituent R' or with multiple substituents R'. When there are multiple (at least 2) substituents R', they may be the same or different substituents. When the same expressions are mentioned below, they have the same meaning. Unless otherwise specified, the selection range of R' is as shown above and will not be repeated.

[0031] The molecular structure of the organic compound provided by the present invention is shown in Formula I, and its parent core structure contains a boron nitrogen multiple resonance (BN-MR) structure, showing good thermally activated delayed fluorescence (TADF) characteristics; at the same time, a specific pyrene group R with a lower triplet energy level is introduced into the BN multiple resonance structure. X , through the pyrene group R X The mutual complexation with the parent core structure plays a role in reducing the triplet energy level and adjusting the light color, so that the organic compound has excellent electroluminescent properties and can provide triplet excitons to achieve higher luminous efficiency. At the same time, based on its excellent carrier transfer efficiency, it is suitable as a luminescent dye (dopant material), especially as a green luminescent dye, which gives the organic electroluminescent device higher luminous efficiency, longer life and lower voltage, and effectively improves the overall performance of the device.

[0032] It should be noted that, in order to facilitate explanation, the possible effects of each group / feature are described separately in the present invention, but this does not mean that these groups / features act in isolation. In fact, the essential reason for obtaining good performance is the optimized combination of the entire molecular structure, which is the result of the synergistic effect of each group, rather than the effect of a single group / feature.

[0033] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0034] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. The same descriptions below have the same meanings.

[0035] In the present invention, the expression of chemical elements, unless otherwise specified, includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes 1 H (hydrogen), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C. 13 C, etc.

[0036] In the present invention, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0037] In the present invention, the expression of a ring structure crossed by “—” indicates that the connection site is at any position on the ring structure that can form a bond.

[0038] In the present invention, "*" indicates the attachment point of the group.

[0039] In the present invention, the expression of Ca-Cb means that the number of carbon atoms in the group is ab. Unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms in the substituent.

[0040] In the present invention, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0041] In the present invention, C1-C20 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0042] The C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0043] The C2-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0044] The C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0045] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0046] The C6-C60 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0047] The C3-C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0048] The C4-C60 can all be C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0049] In the present invention, the C1-C20 straight chain or branched alkyl group, preferably a C1-C16 straight chain or branched alkyl group, and further preferably a C1-C10 straight chain or branched alkyl group, illustratively includes but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0050] Specific examples of the C1-C20 alkoxy group include monovalent groups obtained by connecting the above-mentioned linear or branched alkyl groups to O.

[0051] A specific example of the C1-C20 alkylsilyl group is a monovalent group in which at least one hydrogen in -SiH3 is replaced by the above-mentioned straight-chain or branched alkyl group; a specific example of the C1-C20 alkylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above-mentioned straight-chain or branched alkyl group.

[0052] The C3-C20 cycloalkyl, preferably C3-C10 cycloalkyl, includes monocycloalkyl or polycycloalkyl. Monocycloalkyl refers to an alkyl group containing a single cyclic structure, and polycycloalkyl refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on the ring; exemplary examples include but are not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0053] The C2-C20 alkenyl, preferably C2-C10 alkenyl, contains at least one C=C, illustratively including but not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl and the like.

[0054] In the present invention, the C6-C60 aryl group, preferably a C6-C30 aryl group, and more preferably a C6-C20 aryl group, includes a monocyclic aryl group and a condensed aryl group; the monocyclic aryl group means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are connected by a single bond, and exemplary examples include but are not limited to: phenyl, biphenyl, terphenyl, quaterphenyl, etc.; the condensed aryl group means that the group contains at least two aromatic rings, and the aromatic rings share two The group in which adjacent carbon atoms are fused to each other includes, but is not limited to, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl, perylene, It should be noted that the monocyclic aromatic groups and condensed aromatic groups connected by a single bond also belong to the scope of aromatic groups, such as phenylnaphthyl, naphthylphenyl, naphthylnaphthyl, phenylnaphthylphenyl, etc.

[0055] The C3-C60 heteroaryl, preferably C6-C30 heteroaryl, further preferably C3-C20 heteroaryl, includes a monocyclic heteroaryl or a condensed ring heteroaryl. The monocyclic heteroaryl means that the molecule contains at least one heteroaryl. When the molecule contains a heteroaryl and other groups (such as aryl, heteroaryl, etc.), the heteroaryl and other groups are connected by a single bond, exemplarily including but not limited to: pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, etc. The fused ring heteroaryl group means a group containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two groups share two adjacent atoms fused to each other, including but not limited to: quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolcarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc. It should be noted that heteroaryl and heteroaryl connected by a single bond, aryl and heteroaryl connected by a single bond also belong to the scope of heteroaryl, such as phenylpyridyl, phenylpyrimidinyl, diphenylpyridinyl, diphenylpyrimidinyl, etc.

[0056] In the present invention, the C6-C30 aryloxy group is a monovalent group formed by connecting the above-mentioned aryl groups and O, and the C3-C30 heteroaryloxy group is a monovalent group formed by connecting the above-mentioned heteroaryl groups and O.

[0057] In the present invention, a specific example of the C6-C30 arylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above aryl group, including but not limited to phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, biphenylamino, etc. A specific example of the C3-C30 heteroarylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above heteroaryl group, including but not limited to pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0058] A specific example of the C6-C30 arylsilyl group is a monovalent group in which at least one hydrogen in -SiH3 is replaced by the above-mentioned aryl group.

[0059] Preferably, Ar1 is Thus, the organic compound has a structure as shown in Formula II:

[0060]

[0061] Wherein, X1, X2, X3, X4, Y1, Y2, Y3, Y4, Z1, Z2, Z3, Ar2 have the same defined ranges as in Formula I;

[0062] X5, X6, X7, X8, and X9 are each independently selected from CR A4 or N; multiple (e.g. 2, 3, 4, 5) CR A4 R A4 are the same or different groups.

[0063] R A4 each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; two adjacent R A4 They are not connected or connected to form a ring through chemical bonds; R A4 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.

[0064] More preferably, the X 9 CR A4 , X 9 R A4 The adjacent ring structure is connected to form a ring through a chemical bond Y', and the organic compound has a structure as shown in Formula III-A:

[0065]

[0066] wherein X1, X2, X3, X4, X5, X6, X7, X8, Y1, Y2, Y3, Y4, Z1, Z2, Z3, and Ar2 have the same defined ranges as in Formula II.

[0067] The Y' is selected from a single bond, O, S, Se, NAr 11 , CR 11 R 12 or SiR 13 R 14 Any one of the above, more preferably a single bond. Wherein, when Y' is selected from a single bond, it represents that the ring where Y' is located is a five-membered ring (the ring where Y' and N are located is a pyrrole ring).

[0068] Ar 11 Any one selected from an unsubstituted or R'-substituted C6-C60 aryl group and an unsubstituted or R'-substituted C3-C60 heteroaryl group.

[0069] R 11 , R 12 , R 13 , R 14 are each independently selected from any one of hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the R 11 With R 12 are not connected or connected to form a ring through chemical bonds, the R 13 With R 14 They are not connected to each other or are connected to form a ring through chemical bonds.

[0070] Preferably, X 9 With X 4 The organic compound is connected to form a ring by a single bond, and has a structure as shown in Formula III-B:

[0071]

[0072] wherein X1, X2, X3, X4, X5, X6, X7, X8, Y1, Y2, Y3, Y4, Z1, Z2, Z3, and Ar2 have the same defined ranges as in Formula II.

[0073] Preferably, any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 Any two adjacent R A4 At least one group of them is connected by a chemical bond to form a ring E, and the ring E has a structure as shown in formula a:

[0074]

[0075] In formula a, the dotted line represents a fused bond.

[0076] In formula a, X 11 , X 12 , X 13 , X 14 Each independently selected from CR C1 or N; multiple (e.g. 2, 3, 4) CR C1 R C1 are the same or different groups.

[0077] R C1 R is each independently selected from any one of hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R C1 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.

[0078] In formula a, M1 is selected from O, S, Se, N-Ar 21 or SiR 21 R 22 Any one of .

[0079] In formula a, M2 is selected from single bond, O, S, Se, N-Ar 22 , CR 23 R 24 or SiR 25 R 26 any one of; it should be noted that, when M2 is a single bond, the ring E shown in formula a can be understood as a structure in which a six-membered ring (such as a benzene ring) and a five-membered ring (such as a pyrrole ring, a furan ring, or a thiophene ring) are fused; when M2 is not a single bond, the ring E shown in formula a can be understood as a structure in which two six-membered rings are fused.

[0080] Ar 21 ,Ar 22 Each is independently selected from any one of an unsubstituted or R'-substituted C6-C60 aryl group and an unsubstituted or R'-substituted C3-C60 heteroaryl group.

[0081] R 21 , R 22 , R 23 , R 24 , R 25 , R 26are each independently selected from any one of hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the R 21 With R 22 are not connected or connected to form a ring through chemical bonds, the R 23 With R 24 are not connected or connected to form a ring through chemical bonds, the R 25 With R 26 They are not connected to each other or are connected to form a ring through chemical bonds.

[0082] Preferably, the M1 is selected from O, S, Se, N-Ar 21 or SiR 21 R 22 Any one of: wherein M2 is a single bond, and thus, the ring F is

[0083] Preferably, any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 Any two adjacent R A4 Up to four groups in the ring are connected by chemical bonds to form ring E.

[0084] Preferably, any two adjacent R A1 Any two adjacent R A4 A group of R is connected by chemical bonds to form ring E; and / or any two adjacent R A2 A group of them are connected by chemical bonds to form ring E.

[0085] Preferably, any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 Any two adjacent R A4 A group of them are connected by chemical bonds to form ring E.

[0086] Preferably, the organic compound has a structure as shown in any one of Formula IV-1 to Formula IV-14:

[0087]

[0088]

[0089]

[0090] Among them, M1, X 11 , X 12 , X 13 , X 14 It has the same defined range as in formula a; X1, X2, X3, X5, X6, X7, X8, Y1, Y2, Y3, Y4, Z1, Z2, Z3, Ar2 have the same defined range as in formula I.

[0091] Preferably, the organic compound has a structure as shown in any one of Formula IV-1, Formula IV-2, Formula IV-3, Formula IV-4, Formula IV-5, Formula IV-6, Formula IV-11, and Formula IV-12, and further preferably has a structure as shown in any one of Formulas IV-1 to IV-4.

[0092] Preferably, Ar2 is represents the attachment site of the group, Y5, Y6, Y7, Y8, Y9 are each independently selected from CR A5 or N; R A5 With R A1 The same range, R A5 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.

[0093] Preferably, the organic compound has a structure as shown in Formula II-B:

[0094]

[0095] More preferably, Y9 is CR A5 , R in Y9 A5 It is not connected to the adjacent ring structure or is connected to form a ring through a single bond.

[0096] Preferably, the organic compound has a structure as shown in any one of Formula V-1 to Formula V-14:

[0097]

[0098]

[0099]

[0100] Wherein, the dashed line represents a single bond or no connection.

[0101] It is understood that in the structures shown in Formula V-1 to Formula V-10, the single bond shown by the dotted line may or may not exist; when the dotted line represents a single bond, it means that the rings are connected to form a ring through a single bond; when the dotted line represents no connection, that is, the chemical bond shown by the dotted line does not exist. When the same description is involved below, it has the same meaning and will not be repeated one by one.

[0102] M1, X 11 , X 12 , X 13 , X 14 It has the same defined range as in formula a; X1, X2, X3, X5, X6, X7, X8, Y1, Y2, Y3, Y4, Z1, Z2, and Z3 have the same defined range as in formula I.

[0103] Y5, Y6, Y7, Y8, and Y9 are each independently selected from CR A5 or N; multiple (e.g. 2, 3, 4, 5) CR A5 R A5 are the same or different groups.

[0104] R A5 each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; two adjacent R A5 They are not connected or connected to form a ring through chemical bonds; R A5 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.

[0105] Preferably, the organic compound has a structure as shown in any one of Formula V-1, Formula V-2, Formula V-3, Formula V-4, Formula V-5, Formula V-6, Formula V-11, and Formula V-12, and further preferably has a structure as shown in any one of Formulas V-1 to V-4.

[0106] In the present invention, X1, X2, X3, X5, X6, X7, X8, Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, Y9, Z1, Z2, and Z3 can all be X (Pyrene group) is connected by a carbon-carbon single bond.

[0107] Preferably, at least one of X5, X6, X7, Y2, Y3, Y5, Y6, Y7, Y8, Y9, Z1, Z2, and Z3 is CR XIt is further preferred that at least one of X6, X7, Y2, Y3, Y6, Y8, Y9, Z1, Z2, and Z3 is CR X .

[0108] Preferably, at least one of Y2, Y3, Y6, Y8, Y9, Z1, Z2 and Z3 is CR X .

[0109] Preferably, at least one of Z1, Z2 and Z3 is CR X

[0110] Preferably, Z2 is CR X .

[0111] Preferably, at most one (0 or 1) of X1, X2, and X3 is N; and / or at most one (0 or 1) of X5, X6, X7, and X8 is N.

[0112] Preferably, X1, X2, and X3 are each independently CR A1 ; and / or, X5, X6, X7, X8 are each independently CR A4 .

[0113] Preferably, the R A1 , R A4 Each is independently selected from hydrogen, fluorine, cyano, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C5-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C2-C10 alkylamino, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6 -C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, further preferably hydrogen, cyano, substituted or unsubstituted C1-C5 straight or branched alkyl, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C6-C20 arylamino, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl.

[0114] In another preferred technical solution, the R A1 , R A4each independently selected from hydrogen, substituted or unsubstituted C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, substituted or unsubstituted C3-C10 (e.g. C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g. C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted Or any one of unsubstituted C6-C20 (for example, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, substituted or unsubstituted C3-C20 heteroaryl (for example, C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.), further preferably any one of hydrogen, C1-C6 straight chain or branched alkyl.

[0115] Preferably, X1, X2 and X3 are CH; and / or, X5, X6, X7 and X8 are CH.

[0116] Preferably, the X 11 , X 12 , X 13 and X 14 There is at most 1 (0 or 1) in N.

[0117] Preferably, the X 11 , X 12 , X 13 , X 14 Each independently is CR C1 .

[0118] Preferably, the R C1 each independently selected from hydrogen, substituted or unsubstituted C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, substituted or unsubstituted C3-C10 (e.g. C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g. C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted Or any one of unsubstituted C6-C20 (for example, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, substituted or unsubstituted C3-C20 heteroaryl (for example, C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.), further preferably any one of hydrogen, C1-C6 straight chain or branched alkyl.

[0119] Preferably, the X 11 , X 12 , X 13 and X 14 All are CH.

[0120] Preferably, at most one (0 or 1) of Y1, Y2, and Y3 is N; and / or at most one (0 or 1) of Y5, Y6, Y7, and Y8 is N.

[0121] Preferably, Y1, Y2, and Y3 are each independently CR A2 .

[0122] Preferably, the number of CH in Y1, Y2 and Y3 is 1-3, for example, the number of CH can be 1, 2 or 3.

[0123] Preferably, Y1 is CH, and Y2 and Y3 are each independently CR A2 .

[0124] Preferably, the R A2 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and more preferably hydrogen, substituted or unsubstituted substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylamino, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, and further preferably hydrogen, substituted or unsubstituted any one of the following groups: C1-C6 straight or branched alkyl, trimethylsilyl, diphenylamino, phenyl, naphthyl, anthracenyl, biphenyl, terphenyl, pyridyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, fluorenyl.

[0125] Preferably, Y5, Y6, Y7, and Y8 are each independently selected from CR A5 .

[0126] Preferably, the number of CHs in Y5, Y6, Y7 and Y8 is 1-4, for example, the number of CHs may be 1, 2, 3 or 4.

[0127] Preferably, when the dashed lines in formula V-1 to V-10 represent absence, one of Y6 and Y8 is CR A5 or, when the dotted line in formula V-1 to formula V-10 represents a single bond, one of Y6 and Y7 is CR A5 .

[0128] Preferably, in formula V-11 to formula V-14, one of Y6, Y8 and Y9 is CR A5 .

[0129] Preferably, the R A5 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and more preferably hydrogen, substituted or unsubstituted substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylamino, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, and further preferably hydrogen, substituted or unsubstituted any one of the following groups: C1-C6 straight or branched alkyl, trimethylsilyl, diphenylamino, phenyl, naphthyl, anthracenyl, biphenyl, terphenyl, pyridyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, fluorenyl.

[0130] Preferably, at most one (0 or 1) of Z1, Z2 and Z3 is N.

[0131] Preferably, Z1, Z2, and Z3 are each independently CR A3 .

[0132] Preferably, the number of CH in Z1, Z2 and Z3 is 1-2.

[0133] Preferably, the R A3 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, and substituted or unsubstituted C6-C30 aryl, and more preferably hydrogen, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, substituted or unsubstituted The present invention is any one of the substituted C3-C20 (for example, C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl groups, and further preferably any one of hydrogen, substituted or unsubstituted C1-C6 straight chain or branched alkyl, phenyl, naphthyl, anthracenyl, pyrenyl, biphenyl, terphenyl, pyridyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl and fluorenyl.

[0134] Preferably, the organic compound has a structure as shown in any one of Formula VI-1, Formula VI-2, Formula VI-3, Formula VI-4, Formula VI-5, and Formula VI-6:

[0135] Wherein, the dotted line represents a single bond or no connection. When the dotted line represents a single bond, it means that the rings are connected to form a ring through a single bond; when the dotted line represents no connection, the chemical bond shown by the dotted line does not exist.

[0136] M1 is selected from O, S or N-Ar 21 Any one of .

[0137] Z' is selected from O, S, N-Ar 31 、P-Ar 32 , CR 31 R 32 or SiR 33 R 34 Any one of .

[0138] Ar 21 ,Ar 31 ,Ar 32Each is independently selected from any one of an unsubstituted or R'-substituted C6-C60 aryl group, an unsubstituted or R'-substituted C3-C60 heteroaryl group, preferably an unsubstituted or R'-substituted C6-C20 (for example, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl group, and further preferably an unsubstituted or R'-substituted phenyl group, an unsubstituted or R'-substituted biphenyl group, and an unsubstituted or R'-substituted naphthyl group.

[0139] Preferably, Ar 21 ,Ar 31 ,Ar 32 The R's are each independently selected from C1-C6 (eg, C2, C3, C4, C5, etc.) straight or branched alkyl groups, and more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, tert-pentyl, etc.

[0140] R 31 , R 32 , R 33 , R 34 are each independently selected from any one of hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the R 31 With R 32 are not connected or connected to form a ring through chemical bonds, the R 33 With R 34 They are not connected to each other or are connected to form a ring through chemical bonds.

[0141] Preferably, the R 31 , R 32 , R 33 , R 34 Each is independently selected from hydrogen, unsubstituted or R'-substituted C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, unsubstituted or R'-substituted C2-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, unsubstituted or R'-substituted C6-C20 (e.g. C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and any one of hydrogen, methyl, phenyl, biphenyl and naphthyl is further preferred.

[0142] R A1 , R A2 , R A3 , R A4 , R A5 Each independently represents no substitution, monosubstitution to the maximum allowed substitution.

[0143] Among them, R A1 Indicates no substitution (R A1 is hydrogen), monosubstituted, disubstituted, trisubstituted or tetrasubstituted; when R A1 When it represents di-, tri- or tetra-substitution, multiple R A1 are the same or different groups; R A2 , R A3 , R A4 , R A5 The statement is the same, and for the sake of brevity, I will not repeat it.

[0144] R A1 , R A2 , R A3 , R A4 , R A5 R is independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; A1 , R A2 , R A3 , R A4 , R A5 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.

[0145] The R A1 , R A2 , R A3 , R A4 and R A5 At least one of the groups is R X .

[0146] Preferably, the R A3 For the group R X .

[0147] Preferably, the R A1 , R A2 , R A3 , R A4 , R A5 are each independently selected from hydrogen, R X, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) C8, C9, etc.) alkylsilyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) arylamino, substituted or unsubstituted C6-C12 (e.g., C6, C9, C10 or C12, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl.

[0148] Preferably, the R A1 , R A2 , R A4 , R A5 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C12 aryl, and substituted or unsubstituted C3-C20 heteroaryl, and is further preferably hydrogen, substituted or unsubstituted C1-C6 straight or branched alkyl, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, and fluorenyl.

[0149] Preferably, R A1 , R A2 , R A4 , R A5 The substituted substituents are each independently selected from any one of halogen, cyano, unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C2-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl, and further preferably any one of fluorine, cyano, methyl, ethyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl, naphthyl, and carbazolyl.

[0150] Preferably, R A1 , R A2 , R A4 , R A5 The substituted substituents are independently not connected to the adjacent ring structure or are connected by chemical bonds to form a ring Cy1; the ring Cy1 is selected from any one of a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) alicyclic ring, a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic ring, and a substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaromatic ring; further preferably, the ring Cy1 is selected from Any one of the above; the dotted line represents the fusion site of ring Cy1.

[0151] Preferably, the R A1 , R A2 , R A4 , R A5 are independently selected from hydrogen, methyl, ethyl,

[0152] Any one of .

[0153] Preferably, the R A3 For R X .

[0154] Preferably, said L is a single bond, whereby said R X for

[0155] Preferably, the R 1 , R 2 Each independently represents unsubstituted or monosubstituted.

[0156] Preferably, the R 1 , R 2Each is independently selected from any one or a combination of at least two of hydrogen, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, preferably hydrogen, any one of C1-C6 straight or branched alkyl, more preferably hydrogen, methyl, ethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-pentyl.

[0157] Preferably, the R X Selected from Any one of .

[0158] Preferably, the organic compound has a structure as shown in any one of the following S1-S183:

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174] In a second aspect, the present invention provides a use of the organic compound as described in the first aspect, wherein the organic compound is applied to an organic electronic device.

[0175] Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner or electronic paper, and an organic electroluminescent device is further preferred.

[0176] Preferably, the organic compound is applied to an organic electroluminescent device.

[0177] Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

[0178] Preferably, all organic compounds are used as dyes (also known as "doping materials", "dopants", "guest materials") of the light-emitting layer in organic electroluminescent devices.

[0179] In another preferred technical solution, the organic compound can also be used as a sensitizer together with the host material and the dye to achieve a good luminescence effect.

[0180] In a third aspect, the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprises at least one organic compound as described in the first aspect.

[0181] Preferably, the organic layer includes at least one organic compound having a structure shown in S1-S183.

[0182] Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one organic compound as described in the first aspect, and further preferably includes at least one organic compound with a structure shown in S1-S183.

[0183] Preferably, the light-emitting layer comprises a host material and a dye, and the dye comprises at least one organic compound as described in the first aspect.

[0184] In another preferred technical solution, the organic compound provided by the present invention can also be used as a sensitizer together with the host material and the dye to achieve a good luminescence effect.

[0185] Preferably, the mass percentage of the dye in the light-emitting layer is 0.1-10%, for example, it can be 0.2%, 0.5%, 0.8%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 8% or 9%.

[0186] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0187] Preferably, the hole transport region includes any one of a hole injection layer, a hole transport layer, and an electron blocking layer, or a combination of at least two of them.

[0188] Preferably, the electron transport region includes any one of an electron injection layer, an electron transport layer, and a hole blocking layer, or a combination of at least two of them.

[0189] In a preferred technical solution, the organic electroluminescent device (OLED device) includes a first electrode and a second electrode, and an organic layer located between the electrodes. The organic layer can be divided into multiple regions, for example, including a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer includes at least one organic compound as described in the first aspect, and further preferably includes at least one organic compound having a structure shown in S1-S183.

[0190] In a preferred technical solution, the organic electroluminescent device includes a first electrode, a plurality of light-emitting functional layers (organic layers) and a second electrode arranged in sequence; the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer arranged in sequence, and the hole injection layer is in contact with the first electrode (anode). The organic layer (preferably the light-emitting layer) contains at least one organic compound as described in the first aspect, and further preferably contains at least one organic compound having a structure shown in S1-S183.

[0191] In a preferred technical solution, a substrate can be used below the first electrode or above the second electrode. The substrate is glass or polymer material with excellent mechanical strength, thermal stability, water resistance and transparency. In addition, a thin film transistor (TFT) can also be provided on the substrate used as a display.

[0192] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as a cathode, a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0193] The organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic layer can be an organic small molecule, an organic macromolecule or a polymer, and a combination thereof.

[0194] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0195] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include the compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0196]

[0197]

[0198]

[0199] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more compounds of HT-1 to HT-51 above, or one or more compounds of HI-1 to HI-3 below; or one or more compounds of HT-1 to HT-51 can be doped with one or more compounds of HI-1 to HI-3 below.

[0200]

[0201] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra and a host material (Host). The light-emitting layer can be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors can be arranged in a plane according to a pixel pattern, or they can be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0202] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0203]

[0204] In one aspect of the present invention, the light-emitting layer adopts the technology of combining phosphorescence sensitized luminescence and thermally activated sensitized fluorescence luminescence. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of the following PH-1 to PH-85.

[0205]

[0206]

[0207]

[0208]

[0209] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but not limited to, one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds PH-47 to PH-77 described above; or a mixture of, but not limited to, one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.

[0210] The OLED organic layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multi-layer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0211] In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0212]

[0213]

[0214]

[0215]

[0216] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be, but not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0217] The device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes but is not limited to one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, and Yb.

[0218] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0219] Preferably, the display device includes a display screen or a display panel.

[0220] The present invention also provides an electronic device, which includes the above-mentioned display device.

[0221] Compared with the prior art, the present invention has the following beneficial effects:

[0222] In the organic compound provided by the present invention, the boron nitrogen multi-resonance mother core structure and the specific pyrene group R X The design and mutual compounding play the role of reducing the triplet energy level and adjusting the light color, so that the organic compound has excellent electroluminescent performance, can provide triplet excitons to achieve higher luminous efficiency, is suitable for being used as a luminescent dye, especially a green luminescent dye, and can effectively improve the carrier transfer efficiency, so that the organic electroluminescent device containing it has higher luminous efficiency, longer service life and lower voltage, thereby improving the comprehensive performance of the device and fully meeting the requirements for high-performance materials in the current panel and display manufacturing. DETAILED DESCRIPTION

[0223] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0224] In one embodiment, the organic compound has a structure as shown in Formula III-B, wherein Z2 is CR X , the organic compound can be prepared by the following synthetic route:

[0225]

[0226]

[0227] Wherein, X1, X2, X3, X5, X6, X7, X8, Y1, Y2, Y3, Y4, Z1, Z3, Ar2 have the same limited range as formula III-B; Hal1 is selected from any one of I, Br, or Cl, Hal2 is selected from any one of Br or Cl; Hal3 is selected from any one of F, Br, or I; wherein, when Hal3 is F, the atomic number of Hal1 is greater than or equal to Hal2, and when Hal3 is not F, the atomic number of Hal3 is greater than the atomic numbers of Hal1 and Hal2. n-BuLi represents n-butyl lithium, and t-BuLi represents tert-butyl lithium.

[0228] The specific preparation method of the organic compound of the present invention will be described in detail below using a plurality of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples.

[0229] It should be noted that obtaining the organic compound is not limited to the synthesis method and raw materials used in the present invention, and those skilled in the art may also select other methods or routes to obtain the compound proposed in the present invention. The compounds of the synthesis method not mentioned in the present invention are raw materials obtained from commercial channels, or are prepared by these raw materials according to known methods.

[0230] The analysis and detection of the intermediates and target products in the following synthesis examples of the present invention were performed using an ABSCIEX mass spectrometer (4000QTRAP) using matrix-assisted laser desorption ionization (MALDI) technology.

[0231] Synthesis Example 1: Synthesis of organic compound S1

[0232]

[0233]

[0234] (1) Synthesis of intermediate M1-1

[0235] At room temperature, raw material 1 (50 g, 273.26 mmol), raw material 2 (83.99 g, 300.58 mmol), cesium carbonate (133.55 g, 409.88 mmol), N,N-dimethylformamide (DMF, 500 mL) as solvent were added to a 1L single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 100°C overnight. After the reaction solution was cooled, water (500 mL) was added to precipitate a white solid, and stirred for 30 min. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 95 g of white solid M1-1, with a yield of 78.6%. The molecular ion mass determined by mass spectrometry is: 441.21 (theoretical value: 441.14).

[0236] (2) Synthesis of intermediate M1-2

[0237] At room temperature, add raw material M1-1 (30 g, 67.81 mmol), raw material 3 (22.54 g, 67.81 mmol), cesium carbonate (33.14 g, 101.72 mmol), DMF (200 mL) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110°C overnight. After the reaction solution is cooled, add water (500 mL) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 42 g of white solid M1-2, with a yield of 82.1%. The molecular ion mass determined by mass spectrometry is: 753.32 (theoretical value: 753.27).

[0238] (3) Synthesis of intermediate M1-3

[0239] At room temperature, M1-3 (30 g, 39.75 mmol) and xylene (100 mL) were added to a 500 mL three-necked flask, and nitrogen was replaced 3 times. At -70 ° C, tert-butyl lithium n-hexane solution (32.3 mL, 51.67 mmol, 1.6 M) was added to the system, stirred at room temperature for 5 min, heated to 60 ° C for 2 h, and the system changed from anhydrous clear to dark red. Boron tribromide (7.7 mL, 79.49 mmol, 2.60 g / mL) was added to the system at -40 ° C, and stirred at low temperature for 10 min. The system changed from dark red transparent to red turbid. Then N, N-diisopropylethylamine (20.8 mL, 119.24 mmol, 0.74 g / mL) was added at -40 ° C, and the temperature was raised to 120 ° C for overnight reaction. The system was cooled to room temperature, dichloromethane (200 mL) was added to dissolve, and the mixture was concentrated by silica gel chromatography (petroleum ether PE: dichloromethane DCM = 20:1). The crude product was recrystallized twice from toluene / ethanol to obtain 10 g of a red solid with a yield of 34.6%. The molecular ion mass determined by mass spectrometry was 727.32 (theoretical value: 727.29).

[0240] (4) Synthesis of target product S1

[0241] At room temperature, raw material M1-3 (2 g, 2.75 mmol), raw material 4 (0.81 g, 3.3 mmol), tetrakis(triphenylphosphine)palladium (0.09 g, 0.08 mmol), potassium carbonate (0.57 g, 4.12 mmol), 1,4-dioxane (10 mL) and water (2 mL) were added to a 250 mL single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C for 4 h. Cool to room temperature, add 40 mL of water, extract three times with dichloromethane (30 mL), mix the organic phase with silica gel, concentrate, column chromatography (PE: DCM = 20: 1), and recrystallize from toluene / isopropanol to obtain 1.3 g of red solid, with a yield of 52.9%. The molecular ion mass determined by mass spectrometry is: 893.41 (theoretical value: 893.39).

[0242] Synthesis Example 2: Synthesis of Organic Compound S5

[0243]

[0244] At room temperature, raw material M1-3 (2 g, 2.75 mmol, prepared as in Synthesis Example 1), raw material 5 (0.81 g, 3.3 mmol), tetrakis(triphenylphosphine)palladium (0.09 g, 0.08 mmol), potassium carbonate (0.57 g, 4.12 mmol), 1,4-dioxane (10 mL) and water (2 mL) were added to a 250 mL single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C for 4 h. Cool to room temperature, add 40 mL of water, extract three times with dichloromethane (30 mL), mix the organic phase with silica gel, concentrate, column chromatography (PE: DCM = 20: 1), and recrystallize from toluene / isopropanol to obtain 0.8 g of a red solid with a yield of 32.6%. The molecular ion mass determined by mass spectrometry is: 893.43 (theoretical value: 893.39).

[0245] Synthesis Example 3: Synthesis of Organic Compound S11

[0246]

[0247] (1) Synthesis of intermediate M11-1

[0248] At room temperature, raw material M1-1 (30 g, 67.81 mmol, prepared as in Synthesis Example 1), raw material 6 (22.54 g, 67.81 mmol), cesium carbonate (33.14 g, 101.72 mmol), DMF (200 mL) as solvent were added to a 1L single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 110°C overnight. After the reaction solution was cooled, water (500 mL) was added to precipitate a white solid, and stirred for 30 min. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 42 g of white solid M11-1, with a yield of 82.1%. The molecular ion mass determined by mass spectrometry is: 753.32 (theoretical value: 753.27).

[0249] (2) Synthesis of intermediate M11-2

[0250] At room temperature, M11-1 (30 g, 39.75 mmol) and xylene (100 mL) were added to a 500 mL three-necked flask, and nitrogen was replaced 3 times. At -70 °C, tert-butyl lithium n-hexane solution (29.8 mL, 47.7 mmol, 1.6 M) was added to the system, stirred at room temperature for 5 min, heated to 60 °C for reaction for 2 h, and the system changed from anhydrous clear to dark red. Boron tribromide (7.7 mL, 79.49 mmol, 2.60 g / mL) was added to the system at -40 °C, and stirred at low temperature for 10 min. The system changed from dark red transparent to red turbid. Then N, N-diisopropylethylamine (20.8 mL, 119.24 mmol, 0.74 g / mL) was added at -40 °C, and the temperature was raised to 120 °C for reaction overnight. The system was cooled to room temperature, dichloromethane (200 mL) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE:DCM=20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 8.5 g of a red solid with a yield of 29.4%. The molecular ion mass determined by mass spectrometry was 727.31 (theoretical value: 727.29).

[0251] (3) Synthesis of target product S11

[0252] At room temperature, raw material M11-2 (2.75mmol), raw material 6 (0.8g, 3.3mmol), tetrakis(triphenylphosphine)palladium (0.1g, 0.08mmol), potassium carbonate (0.76g, 5.49mmol), 1,4-dioxane (10mL) and water (2mL) were added to a 250mL single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100°C for 4h. Cool to room temperature, add 40mL of water, extract three times with dichloromethane (30mL), mix the organic phase with silica gel, concentrate, column chromatography (PE:DCM=20:1), and recrystallize from toluene / isopropanol to obtain 1.3g of red solid, with a yield of 52.9%. Molecular ion mass determined by mass spectrometry: 893.41 (theoretical value: 893.39) Synthesis Example 4: Synthesis of organic compound S87

[0253]

[0254] (1) Synthesis of intermediate M87-1

[0255] At room temperature, raw material 1 (30 g, 163.95 mmol), raw material 5 (54.5 g, 163.95 mmol), cesium carbonate (80.13 g, 245.93 mmol), DMF (500 mL) as solvent were added to a 1L single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 100°C overnight. After the reaction solution was cooled, water (500 mL) was added to precipitate a white solid, and stirred for 30 min. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 70 g of white solid M87-1, with a yield of 86.2%. The molecular ion mass determined by mass spectrometry is: 494.11 (theoretical value: 494.08).

[0256] (2) Synthesis of intermediate M87-2

[0257] At room temperature, add raw material M87-1 (20 g, 40.37 mmol), raw material 6 (12.65 g, 40.37 mmol), cesium carbonate (19.73 g, 60.56 mmol), DMF (150 mL) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110°C overnight. After the reaction solution is cooled, add water (500 mL) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 25 g of white solid M87-2, with a yield of 78.5%. The molecular ion mass determined by mass spectrometry is: 787.25 (theoretical value: 787.22).

[0258] (3) Synthesis of intermediate M87-3

[0259] At room temperature, M87-2 (25 g, 31.69 mmol) and xylene (100 mL) were added to a 500 mL three-necked flask, and nitrogen was replaced 3 times. At -70 ° C, tert-butyl lithium n-hexane solution (23.77 mL, 38.03 mmol, 1.6 M) was added to the system, stirred at room temperature for 5 min, heated to 60 ° C for 2 h, and the system changed from anhydrous clear to dark red. Boron tribromide (6.11 mL, 63.39 mmol, 2.60 g / mL) was added to the system at -40 ° C, and stirred at low temperature for 10 min. The system changed from dark red transparent to red turbid. Then N, N-diisopropylethylamine (16.6 mL, 98.05 mmol, 0.74 g / mL) was added at -40 ° C, and the temperature was raised to 120 ° C for overnight reaction. The system was cooled to room temperature, dichloromethane (200 mL) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE:DCM=20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 8.3 g of a red solid with a yield of 34.36%. The molecular ion mass determined by mass spectrometry was 761.31 (theoretical value: 761.24).

[0260] (4) Synthesis of target product S87

[0261] At room temperature, raw material M87-3 (2 g, 2.62 mmol), raw material 4 (0.77 g, 3.15 mmol), tetrakis(triphenylphosphine)palladium (0.09 g, 0.079 mmol), potassium carbonate (0.73 g, 5.25 mmol), 1,4-dioxane (10 mL) and water (2 mL) were added to a 250 mL single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C for 4 h. Cool to room temperature, add 40 mL of water, extract three times with dichloromethane (30 mL), mix the organic phase with silica gel, concentrate, column chromatography (PE: DCM = 20: 1), and recrystallize from toluene / isopropanol to obtain 1.2 g of red solid, with a yield of 49.3%. The molecular ion mass determined by mass spectrometry is: 927.37 (theoretical value: 927.34).

[0262] Synthesis Example 5: Synthesis of Organic Compound S90

[0263]

[0264] (1) Synthesis of intermediate M90-1

[0265] At room temperature, add raw material M87-1 (20g, 40.37mmol, prepared as in Synthesis Example 4), raw material 7 (10.43g, 40.37mmol), cesium carbonate (19.73g, 60.56mmol), DMF (150mL) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110°C overnight. After the reaction solution is cooled, add water (500mL) to precipitate a white solid, and stir for 30min. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 23.3g of white solid M90-1, with a yield of 78.7%. The molecular ion mass determined by mass spectrometry is: 732.20 (theoretical value: 732.15).

[0266] (2) Synthesis of intermediate M90-2

[0267] At room temperature, M90-1 (15 g, 20.45 mmol) and xylene (100 mL) were added to a 500 mL three-necked flask, and nitrogen was replaced 3 times. At -70 ° C, tert-butyl lithium n-hexane solution (16.33 mL, 24.53 mmol, 1.6 M) was added to the system, stirred at room temperature for 5 min, heated to 60 ° C for 2 h, and the system changed from anhydrous clear to dark red. Boron tribromide (3.94 mL, 40.89 mmol, 2.60 g / mL) was added to the system at -40 ° C, and stirred at low temperature for 10 min. The system changed from dark red transparent to red turbid. Then N, N-diisopropylethylamine (10.71 mL, 61.34 mmol, 0.74 g / mL) was added at -40 ° C, and the temperature was raised to 120 ° C for overnight reaction. The system was cooled to room temperature, dichloromethane (200 mL) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE:DCM=20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 3 g of red solid, with a yield of 20.8%. The molecular ion mass determined by mass spectrometry was 706.19 (theoretical value: 706.17).

[0268] (3) Synthesis of target product S90

[0269] At room temperature, raw material M90-2 (2 g, 2.83 mmol), raw material 4 (0.84 g, 3.39 mmol), tetrakis(triphenylphosphine)palladium (0.1 g, 0.085 mmol), potassium carbonate (0.78 g, 5.66 mmol), 1,4-dioxane (10 mL) and water (2 mL) were added to a 250 mL single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C for 4 h. Cool to room temperature, add 40 mL of water, extract three times with dichloromethane (30 mL), mix the organic phase with silica gel, concentrate, column chromatography (PE: DCM = 20: 1), and recrystallize from toluene / isopropanol to obtain 1.1 g of red solid, with a yield of 44.6%. The molecular ion mass determined by mass spectrometry is: 972.31 (theoretical value: 872.27).

[0270] Synthesis Example 6: Synthesis of Organic Compound S125

[0271]

[0272] (1) Synthesis of intermediate M125-1

[0273] At room temperature, add raw material M87-1 (15g, 30.28mmol, prepared as in Synthesis Example 4), raw material 8 (7.7g, 30.28mmol), cesium carbonate (14.6g, 45.42mmol), DMF (150mL) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110°C overnight. After the reaction solution is cooled, add water (500mL) to precipitate a white solid, and stir for 30min. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 16.2g of white solid M125-1, with a yield of 73%. The molecular ion mass determined by mass spectrometry is: 731.20 (theoretical value: 731.15).

[0274] (2) Synthesis of intermediate M125-2

[0275] At room temperature, M125-1 (10 g, 13.65 mmol) and xylene (100 mL) were added to a 500 mL three-necked flask, and nitrogen was replaced 3 times. At -70 °C, tert-butyl lithium n-hexane solution (10.24 mL, 16.38 mmol, 1.6 M) was added to the system, stirred at room temperature for 5 min, heated to 60 °C for 2 h, and the system changed from anhydrous clear to dark red. Boron tribromide (2.63 mL, 27.3 mmol, 2.60 g / mL) was added to the system at -40 °C, stirred at low temperature for 10 min, and the system changed from dark red transparent to red turbid. Then N, N-diisopropylethylamine (7.15 mL, 40.95 mmol, 0.74 g / mL) was added at -40 °C, and the temperature was raised to 120 °C for overnight reaction. The system was cooled to room temperature, dichloromethane (200 mL) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20: 1), and the crude product was recrystallized twice from toluene / ethanol to obtain 2.5 g of a red solid with a yield of 25.94%. The molecular ion mass determined by mass spectrometry was 705.22 (theoretical value: 705.18).

[0276] (3) Synthesis of target product S125

[0277] At room temperature, raw material M125-2 (2 g, 2.73 mmol), raw material 4 (0.81 g, 3.28 mmol), tetrakis(triphenylphosphine)palladium (0.1 g, 0.081 mmol), potassium carbonate (0.75 g, 5.46 mmol), 1,4-dioxane (10 mL) and water (2 mL) were added to a 250 mL single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C for 4 h. Cool to room temperature, add 40 mL of water, extract three times with dichloromethane (30 mL), mix the organic phase with silica gel, concentrate, column chromatography (PE: DCM = 20: 1), and recrystallize from toluene / isopropanol to obtain 0.9 g of a red solid with a yield of 37.8%. The molecular ion mass determined by mass spectrometry is: 871.32 (theoretical value: 871.28).

[0278] Synthesis Example 7: Synthesis of Organic Compound S126

[0279]

[0280] (1) Synthesis of intermediate M126-1

[0281] At room temperature, add raw material M1-1 (20 g, 45.21 mmol), raw material 9 (18.03 g, 54.25 mmol), cesium carbonate (29.46 g, 90.42 mmol), DMF (200 mL) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110°C overnight. After the reaction solution is cooled, add water (500 mL) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 27.6 g of white solid M126-1, with a yield of 80.9%. The molecular ion mass determined by mass spectrometry is: 753.29 (theoretical value: 753.27).

[0282] (2) Synthesis of intermediate M126-2

[0283] At room temperature, M126-1 (10 g, 13.26 mmol) and xylene (100 mL) were added to a 500 mL three-necked flask, and nitrogen was replaced 3 times. At -70 °C, tert-butyl lithium n-hexane solution (9.94 mL, 15.9 mmol, 1.6 M) was added to the system, stirred at room temperature for 5 min, heated to 60 °C for 2 h, and the system changed from anhydrous clear to dark red. Boron tribromide (2.55 mL, 26.5, mmol, 2.60 g / mL) was added to the system at -40 °C, stirred at low temperature for 10 min, and the system changed from dark red transparent to red turbid. Then N, N-diisopropylethylamine (6.94 mL, 39.75 mmol, 0.74 g / mL) was added at -40 °C, and the temperature was raised to 120 °C for overnight reaction. The system was cooled to room temperature, dichloromethane (200 mL) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20: 1), and the crude product was recrystallized twice from toluene / ethanol to obtain 2.2 g of a red solid with a yield of 22.8%. The molecular ion mass determined by mass spectrometry was 727.33 (theoretical value: 727.29).

[0284] (3) Synthesis of target product M126

[0285] At room temperature, raw material M126-2 (2.2 g, 3.02 mmol), raw material 4 (0.89 g, 3.63 mmol), tetrakis(triphenylphosphine)palladium (0.1 g, 0.09 mmol), potassium carbonate (0.84 g, 6.04 mmol), 1,4-dioxane (10 mL) and water (2 mL) were added to a 250 mL single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C for 4 h. Cool to room temperature, add 40 mL of water, extract three times with dichloromethane (30 mL), mix the organic phase with silica gel, concentrate, column chromatography (PE: DCM = 20: 1), and recrystallize from toluene / isopropanol to obtain 0.8 g of red solid, with a yield of 29.6%. The molecular ion mass determined by mass spectrometry is: 893.42 (theoretical value: 893.39).

[0286] Synthesis Example 8: Synthesis of Organic Compound S137

[0287]

[0288] (1) Synthesis of intermediate M137-1

[0289] At room temperature, add raw material M87-1 (20 g, 40.37 mmol), raw material 10 (12.65 g, 40.37 mmol), cesium carbonate (19.73 g, 60.56 mmol), DMF (200 mL) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110°C overnight. After the reaction solution is cooled, add water (500 mL) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 26.2 g of white solid M137-1, with a yield of 82.27%. The molecular ion mass determined by mass spectrometry is: 787.26 (theoretical value: 787.22).

[0290] (2) Synthesis of intermediate M137-2

[0291] At room temperature, M137-1 (10 g, 12.68 mmol) and xylene (100 mL) were added to a 500 mL three-necked flask, and nitrogen was replaced 3 times. At -70 °C, tert-butyl lithium n-hexane solution (9.51 mL, 15.21 mmol, 1.6 M) was added to the system, stirred at room temperature for 5 min, heated to 60 °C and reacted for 2 h, and the system changed from anhydrous clear to dark red. Boron tribromide (2.44 mL, 25.36 mmol, 2.60 g / mL) was added to the system at -40 °C, stirred at low temperature for 10 min, and the system changed from dark red transparent to red turbid. Then N, N-diisopropylethylamine (6.64 mL, 38.03 mmol, 0.74 g / mL) was added at -40 °C, and the temperature was raised to 120 °C and reacted overnight. The system was cooled to room temperature, dichloromethane (200 mL) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20: 1), and the crude product was recrystallized twice from toluene / ethanol to obtain 2.3 g of a red solid with a yield of 23.8%. The molecular ion mass determined by mass spectrometry was 761.32 (theoretical value: 761.24).

[0292] (3) Synthesis of target product S137

[0293] At room temperature, raw material M137-2 (2 g, 2.62 mmol), raw material 4 (0.77 g, 3.15 mmol), tetrakis(triphenylphosphine)palladium (0.09 g, 0.08 mmol), potassium carbonate (0.73 g, 5.25 mmol), 1,4-dioxane (10 mL) and water (2 mL) were added to a 250 mL single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C for 4 h. Cool to room temperature, add 40 mL of water, extract three times with dichloromethane (30 mL), mix the organic phase with silica gel, concentrate, column chromatography (PE: DCM = 20: 1), and recrystallize from toluene / isopropanol to obtain 1.1 g of red solid, with a yield of 45.2%. The molecular ion mass determined by mass spectrometry is: 927.41 (theoretical value: 927.34).

[0294] Synthesis Example 9: Synthesis of Organic Compound S168

[0295]

[0296] (1) Synthesis of intermediate M168-1

[0297] At room temperature, raw material 1 (20 g, 109.3 mmol), raw material 9 (36.33 g, 109.3 mmol), cesium carbonate (53.42 g, 163.95 mmol), DMF (500 mL) as solvent were added to a 1L single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 100°C overnight. After the reaction solution was cooled, water (500 mL) was added to precipitate a white solid, and stirred for 30 min. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 42 g of white solid M168-1, with a yield of 77.6%. The molecular ion mass determined by mass spectrometry is: 494.13 (theoretical value: 494.08).

[0298] (2) Synthesis of intermediate M168-2

[0299] At room temperature, add raw material M168-1 (20 g, 40.37 mmol), raw material 10 (16.32 g, 44.41 mmol), cesium carbonate (19.73 g, 60.56 mmol), DMF (300 mL) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110°C overnight. After the reaction solution is cooled, add water (500 mL) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 19.3 g of white solid M168-2, with a yield of 57.3%. The molecular ion mass determined by mass spectrometry is: 841.33 (theoretical value: 841.26).

[0300] (3) Synthesis of intermediate M168-3

[0301] At room temperature, M168-2 (19.5 g, 23.14 mmol) and xylene (100 mL) were added to a 500 mL three-necked flask, and nitrogen was replaced 3 times. At -70 ° C, tert-butyl lithium n-hexane solution (17.35 mL, 27.76 mmol, 1.6 M) was added to the system, stirred at room temperature for 5 min, heated to 60 ° C for reaction for 2 h, and the system changed from anhydrous clear to dark red. Boron tribromide (4.46 mL, 46.27 mmol, 2.60 g / mL) was added to the system at -40 ° C, stirred at low temperature for 10 min, and the system changed from dark red transparent to red turbid. Then N, N-diisopropylethylamine (14.75 mL, 69.41 mmol, 0.74 g / mL) was added at -40 ° C, and the temperature was raised to 120 ° C for reaction overnight. The system was cooled to room temperature, dichloromethane (200 mL) was added to dissolve, and the mixture was concentrated by silica gel chromatography (PE: DCM = 20:1). The crude product was recrystallized twice from toluene / ethanol to obtain 3.5 g of a red solid with a yield of 18.5%. The molecular ion mass determined by mass spectrometry was 815.35 (theoretical value: 815.29).

[0302] (4) Synthesis of target product S168

[0303] At room temperature, raw material M168-3 (3 g, 3.68 mmol), raw material 4 (1.09 g, 4.41 mmol), tetrakis(triphenylphosphine)palladium (0.13 g, 0.11 mmol), potassium carbonate (1.02 g, 7.35 mmol), 1,4-dioxane (10 mL) and water (2 mL) were added to a 250 mL single-mouth bottle as solvents, nitrogen was replaced three times, and the reaction was carried out at 100 ° C for 4 h. Cool to room temperature, add 40 mL of water, extract three times with dichloromethane (30 mL), mix the organic phase with silica gel, concentrate, column chromatography (PE: DCM = 20: 1), and recrystallize from toluene / isopropanol to obtain 1.1 g of a red solid with a yield of 30.5%. The molecular ion mass determined by mass spectrometry is: 981.41 (theoretical value: 981.39).

[0304] Synthesis Example 10: Synthesis of Organic Compound S174

[0305]

[0306] (1) Synthesis of intermediate M174-1

[0307] At room temperature, add raw material M87-1 (40.37 mmol), raw material 11 (16.32 g, 44.41 mmol), cesium carbonate (19.73 g, 60.56 mmol), DMF (300 mL) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110°C overnight. After the reaction solution is cooled, add water (500 mL) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 21.3 g of white solid M174-1, with a yield of 62.6%. The molecular ion mass determined by mass spectrometry is: 841.30 (theoretical value: 841.26).

[0308] (2) Synthesis of intermediate M174-2

[0309] At room temperature, M174-1 (20 g, 23.73 mmol) and xylene (100 mL) were added to a 500 mL three-necked flask, and nitrogen was replaced 3 times. At -70 °C, tert-butyl lithium n-hexane solution (17.8 mL, 28.47 mmol, 1.6 M) was added to the system, stirred at room temperature for 5 min, heated to 60 °C and reacted for 2 h, and the system changed from anhydrous clear to dark red. Boron tribromide (4.57 mL, 47.46 mmol, 2.60 g / mL) was added to the system at -40 °C, stirred at low temperature for 10 min, and the system changed from dark red transparent to red turbid. Then N, N-diisopropylethylamine (12.43 mL, 71.19 mmol, 0.74 g / mL) was added at -40 °C, and the temperature was raised to 120 °C and reacted overnight. The system was cooled to room temperature, dichloromethane (200 mL) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20: 1), and the crude product was recrystallized twice from toluene / ethanol to obtain 3.6 g of a red solid with a yield of 18.6%. The molecular ion mass determined by mass spectrometry was 815.32 (theoretical value: 815.29).

[0310] (3) Synthesis of target product S174

[0311] At room temperature, raw material M174-2 (3 g, 3.68 mmol), raw material 4 (1.09 g, 4.41 mmol), tetrakis(triphenylphosphine)palladium (0.13 g, 0.11 mmol), potassium carbonate (1.02 g, 7.35 mmol), 1,4-dioxane (10 mL) and water (2 mL) were added to a 250 mL single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100 ° C for 4 h. Cool to room temperature, add 40 mL of water, extract three times with dichloromethane (30 mL), mix the organic phase with silica gel, concentrate, column chromatography (PE: DCM = 20: 1), and recrystallize from toluene / isopropanol to obtain 2.1 g of red solid, with a yield of 58.2%. The molecular ion mass determined by mass spectrometry is: 981.43 (theoretical value: 981.39).

[0312] The organic compound of the present invention is used in a light-emitting device and can be used as a doping material for a light-emitting layer. The compound prepared in the above embodiment of the present invention is tested for fluorescence emission spectrum using a Hitachi F-4600 fluorescence spectrophotometer in a toluene solution. The test concentration is 10 -5 mol / L, S1 and T1 are calculated from the wavelengths corresponding to the peaks of the fluorescence emission spectrum and phosphorescence emission spectrum tested at 298K and 77K, respectively. The test results are shown in Table 1:

[0313] Table 1

[0314] Compound FWHM(nm) <![CDATA[S1(eV)]]> <![CDATA[T1(eV)]]> S12 33 2.38 2.01

[0315] The fluorescence emission spectrum peak of S12 obtained by room temperature testing in toluene solution is 521nm, which is located in the green light region.

[0316] Device Example 1

[0317] An organic electroluminescent device comprises an anode (ITO, 150 nm), a hole injection layer (HI-2, 10 nm), a hole transport layer (HT-2, 40 nm), an electron blocking layer (HT-40, 5 nm), a light-emitting layer (BFH-3:S1, 30 nm), a hole blocking layer (ET-23, 5 nm), an electron transport layer (ET-59, 25 nm), an electron injection layer (LiF, 0.5 nm) and a cathode (Al, 150 nm) which are stacked in sequence. The preparation method of the organic electroluminescent device is as follows:

[0318] (1) a glass substrate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone / ethanol mixed solvent, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0319] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 Pa, vacuum evaporate HI-2 on the above anode layer as a hole injection layer, the evaporation rate is 0.1nm / s, and the evaporation film thickness is 10nm;

[0320] (3) vacuum evaporating compound HT-2 on the hole injection layer as a hole transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 40 nm;

[0321] (4) vacuum evaporating compound HT-40 on the hole transport layer as an electron blocking layer, with a total film thickness of 5 nm;

[0322] (5) vacuum evaporating a light-emitting layer on the electron blocking layer, wherein the light-emitting layer includes a main material BFH-3 and a dye (the organic compound S1 provided by the present invention, the doping ratio is 5 wt %, and the mass ratio of the main material to S1 is 95:5), the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 30 nm;

[0323] (6) vacuum evaporating compound ET-23 on the light-emitting layer as a hole blocking layer, with a total evaporation film thickness of 5 nm;

[0324] (7) vacuum evaporating compound ET-59 on the hole blocking layer as an electron transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 20 nm;

[0325] (8) Vacuum evaporation of LiF on the electron transport layer as an electron injection layer with a thickness of 0.5 nm;

[0326] (9) Vacuum-evaporating an Al layer with a thickness of 150 nm on the electron injection layer as the cathode of the device to obtain the organic electroluminescent device.

[0327] Device Examples 2-11, Comparative Examples 1-3

[0328] An organic electroluminescent device, which differs from Example 1 only in that the dye of the light-emitting layer is replaced by the compound in Table 2, and the other structures, materials and preparation methods of the device are the same as those of Example 1.

[0329] The structures of the dyes in Comparative Examples 1-3 are as follows:

[0330]

[0331] Device performance test: Under the same brightness, use a digital source meter and brightness meter to measure the driving voltage and current efficiency of each organic electroluminescent device. Specifically, increase the voltage at a rate of 0.1V per second and measure the brightness of the organic electroluminescent device when it reaches 1000cd / m 2 The voltage at this time is the driving voltage, and the current density at this time is measured at the same time; the external quantum efficiency is measured using an integrating sphere; the test method for LT95 life is as follows: use a brightness meter at 1000cd / m 2 At the same brightness, the current is kept constant and the brightness of the organic electroluminescent device is measured to drop to 950cd / m 2 The time, in h;

[0332] The LT95 life test value of comparative example 1 is recorded as 1, and the LT95 life of each device embodiment and other comparative examples is the ratio of the respective LT95 life test value to the test value of comparative example 1 (relative life); the test results are shown in Table 2:

[0333] Table 2

[0334] Part Number dye Required brightness Voltage (V) Relative lifespan EQE(%) Device Example 1 S1 1000 3.6 2.1 14.6 Device Example 2 S5 1000 3.7 2 14.5 Device Example 3 S11 1000 3.7 1.9 14.4 Device Example 4 S87 1000 3.8 1.7 14.4 Device Example 5 S90 1000 3.9 1.6 14.3 Device Example 6 S125 1000 3.8 1.6 14.2 Device Example 7 S126 1000 3.7 1.8 14.5 Device Example 8 S137 1000 3.9 1.5 14.3 Device Example 9 S168 1000 3.9 1.6 14.2 Device Example 10 S174 1000 3.8 1.7 14.2 Device Example 11 S183 1000 3.7 1.8 14.4 Comparative Example 1 R-1 1000 4.2 1 14 Comparative Example 2 R-2 1000 4.0 1.1 13.8 Comparative Example 3 R-3 1000 4.2 0.9 13.9

[0335] Combined with the performance data in Table 2, it can be seen that the low triplet pyrene substituent is introduced into the structure of the organic compound provided by the present invention, which effectively reduces the triplet energy level of the entire molecule and improves the stability of the device operation, thereby greatly improving the device life; at the same time, the structural stability in the present invention is stronger and more conducive to the balance of carrier transfer, so the efficiency is slightly increased and the voltage is slightly reduced.

[0336] The applicant declares that the present invention uses the above-mentioned embodiments to illustrate the organic compounds and their applications, and the organic electroluminescent devices containing the same, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that The organic compound has a structure as shown in Formula I: Wherein, X1, X2, X3, and X4 are each independently selected from CR A1 or N; Y1, Y2, Y3, and Y4 are each independently selected from CR A2 or N; Z1, Z2, and Z3 are each independently selected from CR A3 or N; R A1 , R A2 , R A3 Each is independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; Ar1 and Ar2 are each independently selected from unsubstituted or R B Substituted C6-C60 aryl, unsubstituted or R B Any one of substituted C3-C60 heteroaryl groups; Ar1 ​​and Ar2 are independently not connected to adjacent ring structures or are connected to form a ring through chemical bonds; R B Each is independently selected from any one of halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; Any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 Any two adjacent R B At least one group of them is connected by a chemical bond to form ring E, and the ring E is selected from any one of substituted or unsubstituted C3-C60 heteroaromatic rings; The R A1 , R A2 , R A3 , R B In the above, the other groups except those forming ring E are independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds; R A1 , R A2 , R A3 、Ring E、R B The substituted substituents are each independently selected from halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 arylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano , nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds; The R A1 , R A2 , R A3 At least one of them is a group R X , and / or, the R B At least one of them is a group R X ; The R X for -* represents the attachment site of the group; L is selected from any one of a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group; R 1 , R 2 Each independently represents no substitution, monosubstitution to the maximum allowed substitution; R 1 , R 2 Each is independently selected from any one or a combination of at least two of hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; The substituents substituted in L are each independently selected from halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 arylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano , nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl, any one of the substituted substituents, each of which is independently not connected to the adjacent ring structure or is connected to form a ring by a chemical bond; R' is independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, or a combination of at least two thereof; adjacent R's are not connected or are connected to form a ring by chemical bonds; the R' is not connected to adjacent ring structures or is connected to form a ring by chemical bonds.

2. The organic compound according to claim 1, characterized in that The organic compound has a structure as shown in Formula II: Wherein, X1, X2, X3, X4, Y1, Y2, Y3, Y4, Z1, Z2, Z3, Ar2 have the same defined ranges as in Formula I; X5, X6, X7, X8, and X9 are each independently selected from CR A4 or N; R A4 each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; two adjacent R A4 They are not connected or connected to form a ring through chemical bonds; R A4 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.

3. The organic compound according to claim 2, characterized in that The organic compound has a structure as shown in Formula III-A: Wherein, X1, X2, X3, X4, X5, X6, X7, X8, Y1, Y2, Y3, Y4, Z1, Z2, Z3, Ar2 have the same defined ranges as in Formula II; Y' is selected from single bond, O, S, Se, NAr 11 , CR 11 R 12 or SiR 13 R 14 Any of the following; Ar 11 Any one selected from unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; R 11 , R 12 , R 13 , R 14 are each independently selected from any one of hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the R 11 With R 12 are not connected or connected to form a ring through chemical bonds, the R 13 With R 14 They are not connected to each other or connected to form a ring through chemical bonds; Preferably, the organic compound has a structure as shown in Formula III-B: wherein X1, X2, X3, X4, X5, X6, X7, X8, Y1, Y2, Y3, Y4, Z1, Z2, Z3, and Ar2 have the same defined ranges as in Formula II.

4. The organic compound according to claim 3, characterized in that Any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 Any two adjacent R A4 At least one group of them is connected by a chemical bond to form a ring E, and the ring E has a structure as shown in formula a: Among them, the dotted lines represent fused bonds; X 11 , X 12 , X 13 , X 14 Each independently selected from CR C1 or N; R C1 R is each independently selected from any one of hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R C1 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; M1 is selected from O, S, Se, N-Ar 21 or SiR 21 R 22 Any of the following; M2 is selected from single bond, O, S, Se, N-Ar 22 , CR 23 R 24 or SiR 25 R 26 Any of the following; Ar 21 ,Ar 22 Each is independently selected from any one of an unsubstituted or R'-substituted C6-C60 aryl group and an unsubstituted or R'-substituted C3-C60 heteroaryl group; R 21 , R 22 , R 23 , R 24 , R 25 , R 26 are each independently selected from any one of hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the R 21 With R 22 are not connected or connected to form a ring through chemical bonds, the R 23 With R 24 are not connected or connected to form a ring through chemical bonds, the R 25 With R 26 They are not connected to each other or connected to form a ring through chemical bonds; Preferably, the M1 is selected from O, S, Se, N-Ar 21 or SiR 21 R 22 Any one of, wherein M2 is a single bond; Preferably, any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 Any two adjacent R A4 Up to four groups in are connected by chemical bonds to form ring E; Preferably, any two adjacent R A1 Any two adjacent R A4 A group of R is connected by chemical bonds to form ring E; and / or any two adjacent R A2 One group of them is connected by chemical bonds to form ring E; Preferably, any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 Any two adjacent R A4 A group of them are connected by chemical bonds to form ring E.

5. The organic compound according to claim 4, characterized in that The organic compound has a structure as shown in any one of Formula IV-1 to Formula IV-14: Among them, M1, X 11 , X 12 , X 13 , X 14 Having the same limited range as in formula a; X1, X2, X3, X5, X6, X7, X8, Y1, Y2, Y3, Y4, Z1, Z2, Z3, Ar2 have the same defined ranges as in Formula I; Preferably, the organic compound has a structure as shown in any one of Formula IV-1, Formula IV-2, Formula IV-3, Formula IV-4, Formula IV-5, Formula IV-6, Formula IV-11, and Formula IV-12, and further preferably has a structure as shown in any one of Formulas IV-1 to IV-4.

6. The organic compound according to claim 5, characterized in that The organic compound has a structure as shown in any one of Formula V-1 to Formula V-14: Among them, the dashed line represents a single bond or no connection; M1, X 11 , X 12 , X 13 , X 14 Having the same limited range as in formula a; X1, X2, X3, X5, X6, X7, X8, Y1, Y2, Y3, Y4, Z1, Z2, Z3 have the same defined ranges as in Formula I; Y5, Y6, Y7, Y8, and Y9 are each independently selected from CR A5 or N; R A5 each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; two adjacent R A5 They are not connected or connected to form a ring through chemical bonds; R A5 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; Preferably, the organic compound has a structure as shown in any one of Formula V-1, Formula V-2, Formula V-3, Formula V-4, Formula V-5, Formula V-6, Formula V-11, and Formula V-12, and further preferably has a structure as shown in any one of Formulas V-1 to V-4.

7. The organic compound according to claim 6, characterized in that At least one of X5, X6, X7, Y2, Y3, Y5, Y6, Y7, Y8, Y9, Z1, Z2, and Z3 is CR X Preferably, at least one of X6, X7, Y2, Y3, Y6, Y8, Y9, Z1, Z2, and Z3 is CR X ; Preferably, at least one of Y2, Y3, Y6, Y8, Y9, Z1, Z2 and Z3 is CR X ; Preferably, Z2 is CR X .

8. The organic compound according to claim 6, characterized in that The X1, X2, and X3 are each independently CR A1 ; and / or, X5, X6, X7, X8 are each independently CR A4 ; Preferably, the R A1 , R A4 Each is independently selected from hydrogen, fluorine, cyano, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C5-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C2-C10 alkylamino, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6 -C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, further preferably hydrogen, cyano, substituted or unsubstituted C1-C5 straight or branched alkyl, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C6-C20 arylamino, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl; Preferably, X1, X2 and X3 are CH; and / or, X5, X6, X7 and X8 are CH; Preferably, the X 11 , X 12 , X 13 , X 14 Each independently is CR C1 ; Preferably, the X 11 , X 12 , X 13 and X 14 All are CH; Preferably, Y1, Y2, and Y3 are each independently CR A2 ; Preferably, the number of CH in Y1, Y2 and Y3 is 1-3; Preferably, Y1 is CH, and Y2 and Y3 are each independently CR A2 ; Preferably, the R A2 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; Preferably, Y5, Y6, Y7, and Y8 are each independently selected from CR A5 ; Preferably, the number of CH in Y5, Y6, Y7 and Y8 is 1-4; Preferably, when the dashed lines in formula V-1 to V-10 represent absence, one of Y6 and Y8 is CR A5 or, when the dotted line in formula V-1 to formula V-10 represents a single bond, one of Y6 and Y7 is CR A5 ; Preferably, in formula V-11 to formula V-14, one of Y6, Y8 and Y9 is CR A5 ; Preferably, the R A5 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; Preferably, Z1, Z2, and Z3 are each independently CR A3 ; Preferably, the number of CH in Z1, Z2 and Z3 is 1-2; Preferably, the R A3 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, and substituted or unsubstituted C6-C30 aryl.

9. The organic compound according to claim 1, characterized in that The organic compound has a structure as shown in any one of Formula VI-1, Formula VI-2, Formula VI-3, Formula VI-4, Formula VI-5, and Formula VI-6: Among them, the dashed line represents a single bond or no connection; M1 is selected from O, S or N-Ar 21 Any of the following: Z' is selected from O, S, N-Ar 31 、P-Ar 32 , CR 31 R 32 or SiR 33 R 34 Any of the following: Ar 21 ,Ar 31 ,Ar 32 Each is independently selected from any one of an unsubstituted or R'-substituted C6-C60 aryl group and an unsubstituted or R'-substituted C3-C60 heteroaryl group; R 31 , R 32 , R 33 , R 34 are each independently selected from any one of hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the R 31 With R 32 are not connected or connected to form a ring through chemical bonds, the R 33 With R 34 They are not connected to each other or connected to form a ring through chemical bonds; R A1 , R A2 , R A3 , R A4 , R A5 Each independently represents no substitution, monosubstitution to the maximum allowed substitution; R A1 , R A2 , R A3 , R A4 , R A5 R is independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; A1 , R A2 , R A3 , R A4 , R A5 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; The R A1 , R A2 , R A3 , R A4 and R A5 At least one of them is a group R X .

10. The organic compound according to claim 9, characterized in that The R A1 , R A2 , R A3 , R A4 , R A5 are each independently selected from hydrogen, R X , any one of substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C6-C20 arylamino, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C3-C20 heteroaryl; Preferably, the R A1 , R A2 , R A4 , R A5 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C12 aryl, and substituted or unsubstituted C3-C20 heteroaryl; Preferably, the R A3 For R X .

11. The organic compound according to any one of claims 1 to 10, characterized in that The L is a single bond; Preferably, the R 1 , R 2 Each independently represents unsubstituted or monosubstituted; Preferably, the R 1 , R 2 Each is independently selected from any one or a combination of at least two of hydrogen, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl, and any one of hydrogen and C1-C6 straight or branched alkyl is further preferred; Preferably, the R X Selected from Any one of .

12. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in any one of the following S1-S183:

13. Use of an organic compound as claimed in any one of claims 1 to 12, characterized in that: The organic compound is applied to organic electronic devices; Preferably, the organic electronic device comprises an organic electroluminescent device; Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

14. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprises at least one organic compound according to any one of claims 1 to 12; Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one organic compound according to any one of claims 1 to 12; Preferably, the light-emitting layer comprises a host material and a doping material, and the doping material comprises at least one organic compound as claimed in any one of claims 1 to 12.

15. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 14.

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